#------------------------------------------------------------------------------
#$Date: 2015-10-01 08:42:04 +0200 (jue 01 de oct de 2015) $
#$Revision: 159086 $
#$URL: svn://www.crystallography.net/cod/cif/7/22/23/7222379.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7222379
loop_
_publ_author_name
'Aksenov, Alexander V.'
'Aksenov, Nicolai A.'
'Orazova, Naila A.'
'Aksenov, Dmitrii A.'
'Dmitriev, Maksim V.'
'Rubin, Michael'
_publ_section_title
;
 Direct metal-free synthesis of diarylamines from 2-nitropropane via the
 twofold C-H functionalization of arenes
;
_journal_name_full               'RSC Adv.'
_journal_paper_doi               10.1039/C5RA17668A
_journal_year                    2015
_chemical_formula_moiety         'C14 H15 N O2'
_chemical_formula_sum            'C14 H15 N O2'
_chemical_formula_weight         229.27
_chemical_name_systematic        bis-(4-methoxyphenyl)-amine
_space_group_IT_number           41
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'C -2ac 2'
_symmetry_space_group_name_H-M   'C 2 c b'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2015-08-10 deposited with the CCDC.
2015-09-30 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.14510(10)
_cell_length_b                   26.7789(5)
_cell_length_c                   7.39200(10)
_cell_measurement_reflns_used    9086
_cell_measurement_temperature    292.89(11)
_cell_measurement_theta_max      73.7020
_cell_measurement_theta_min      5.9640
_cell_volume                     1216.42(3)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35g (release 09-12-2014 CrysAlis171 .NET)
(compiled Dec  9 2014,15:38:47)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35g (release 09-12-2014 CrysAlis171 .NET)
(compiled Dec  9 2014,15:38:47)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35g (release 09-12-2014 CrysAlis171 .NET)
(compiled Dec  9 2014,15:38:47)
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      292.89(11)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed X-ray tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0583
_diffrn_reflns_av_sigmaI/netI    0.0216
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       33
_diffrn_reflns_limit_k_min       -33
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            12894
_diffrn_reflns_theta_full        68.00
_diffrn_reflns_theta_max         74.14
_diffrn_reflns_theta_min         3.30
_exptl_absorpt_coefficient_mu    0.674
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.39591
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35g (release 09-12-2014 CrysAlis171 .NET)
(compiled Dec  9 2014,15:38:47)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.252
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             488
_exptl_crystal_preparation       'RECRYST FROM hexane'
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.131
_refine_diff_density_min         -0.112
_refine_diff_density_rms         0.034
_refine_ls_extinction_coef       0.0020(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.108
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     82
_refine_ls_number_reflns         1156
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.108
_refine_ls_R_factor_all          0.0315
_refine_ls_R_factor_gt           0.0311
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0535P)²+0.1232P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0900
_refine_ls_wR_factor_ref         0.0904
_reflns_number_gt                1134
_reflns_number_total             1156
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            c5ra17668a2.cif
_cod_data_source_block           anna_diaryl_dimethoxy_111
_cod_database_code               7222379
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x+1/2, y, -z+1/2'
'x, -y, -z'
'x+1/2, -y, z+1/2'
'x+1/2, y+1/2, z'
'x+1, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'x+1, -y+1/2, z+1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
H1 H 1.126(6) 0.0000 0.0000 0.093(11) Uiso 1 2 d S
N1 N 0.9908(3) 0.0000 0.0000 0.0553(4) Uani 1 2 d S
C5 C 0.5956(2) -0.10308(5) 0.08133(15) 0.0486(3) Uani 1 1 d .
H5 H 0.4627 -0.1085 0.1382 0.058 Uiso 1 1 calc R
C6 C 0.6877(2) -0.05576(5) 0.07974(15) 0.0477(3) Uani 1 1 d .
H6 H 0.6152 -0.0295 0.1361 0.057 Uiso 1 1 calc R
C2 C 0.9907(2) -0.08662(5) -0.08904(15) 0.0502(3) Uani 1 1 d .
H2 H 1.1226 -0.0813 -0.1476 0.060 Uiso 1 1 calc R
C3 C 0.9007(2) -0.13379(5) -0.08690(16) 0.0525(4) Uani 1 1 d .
H3 H 0.9735 -0.1601 -0.1427 0.063 Uiso 1 1 calc R
C1 C 0.8862(2) -0.04676(4) -0.00440(13) 0.0445(3) Uani 1 1 d .
O1 O 0.6277(2) -0.19044(3) -0.01076(14) 0.0654(3) Uani 1 1 d .
C4 C 0.7033(2) -0.14238(5) -0.00257(15) 0.0487(3) Uani 1 1 d .
C7 C 0.4349(3) -0.20218(6) 0.0842(3) 0.0815(6) Uani 1 1 d .
H7A H 0.4559 -0.1960 0.2109 0.122 Uiso 1 1 calc R
H7B H 0.3998 -0.2368 0.0661 0.122 Uiso 1 1 calc R
H7C H 0.3178 -0.1818 0.0402 0.122 Uiso 1 1 calc R
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
C1 N1 C1 125.67(18) 3
C1 N1 H1 117.17(9) 3
C1 N1 H1 117.17(9) .
C6 C5 C4 119.59(12) .
C6 C5 H5 120.2 .
C4 C5 H5 120.2 .
C5 C6 C1 121.31(11) .
C5 C6 H6 119.3 .
C1 C6 H6 119.3 .
C3 C2 C1 120.77(13) .
C3 C2 H2 119.6 .
C1 C2 H2 119.6 .
C2 C3 C4 120.60(11) .
C2 C3 H3 119.7 .
C4 C3 H3 119.7 .
C6 C1 C2 118.18(12) .
C6 C1 N1 122.98(11) .
C2 C1 N1 118.75(13) .
C4 O1 C7 118.14(11) .
O1 C4 C3 115.72(11) .
O1 C4 C5 124.75(13) .
C3 C4 C5 119.53(12) .
O1 C7 H7A 109.5 .
O1 C7 H7B 109.5 .
H7A C7 H7B 109.5 .
O1 C7 H7C 109.5 .
H7A C7 H7C 109.5 .
H7B C7 H7C 109.5 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N1 C1 1.4079(16) 3
N1 C1 1.4079(16) .
N1 H1 0.83(4) .
C5 C6 1.3879(18) .
C5 C4 1.3893(17) .
C5 H5 0.9300 .
C6 C1 1.390(2) .
C6 H6 0.9300 .
C2 C3 1.3791(19) .
C2 C1 1.3939(18) .
C2 H2 0.9300 .
C3 C4 1.383(2) .
C3 H3 0.9300 .
O1 C4 1.3695(16) .
O1 C7 1.413(2) .
C7 H7A 0.9600 .
C7 H7B 0.9600 .
C7 H7C 0.9600 .
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
C4 C5 C6 C1 0.03(17) .
C1 C2 C3 C4 0.84(19) .
C5 C6 C1 C2 0.48(17) .
C5 C6 C1 N1 -176.23(10) .
C3 C2 C1 C6 -0.91(17) .
C3 C2 C1 N1 175.94(10) .
C1 N1 C1 C6 -32.59(9) 3
C1 N1 C1 C2 150.72(11) 3
C7 O1 C4 C3 175.47(14) .
C7 O1 C4 C5 -5.12(19) .
C2 C3 C4 O1 179.13(11) .
C2 C3 C4 C5 -0.31(18) .
C6 C5 C4 O1 -179.51(11) .
C6 C5 C4 C3 -0.12(17) .
